From Ask Jeeves to AI: How Deep Research Is Transforming Investing
Back in 2002, I was a freshly minted equity analyst at A.G. Edwards. My “deep research” toolkit? Yahoo search, FactSet, the Value Line binders in the library, limited access to a shared Bloomberg terminal, and a telephone. Every quarter, I’d cold call self-storage operators to check pricing trends, or brokers to get a gut read on leasing velocity in secondary markets. It was gritty, time-consuming… and honestly, pretty fun. I learned more in that job than any other.
Fast forward to 2025. The tools have changed, but the job hasn’t: get smarter, faster than the market. With information now ubiquitous, the only edge left is how you use it. In the family office and lower middle market space, our edge is in how we synthesize complex data and, most importantly, how we underwrite people. Because as I’ve written before: good people build great companies. Financials are just a byproduct.
The Evolution of Deep Research
What used to take weeks now happens in minutes. Today, I can hold a 45-minute conversation with an AI assistant (usually ChatGPT, occasionally Gemini or Claude) about:
· Who dominates transmission remanufacturing in Dallas
· How a target’s 12-month EBITDA compares to regional comps
· Which franchising models offer the best IRR for operators with limited capital
· How union exposure might impact an acquisition
· Or even, what Marcus Aurelius might say about deal structuring
It’s not just the speed, it’s the breadth of information. I don’t use AI to replace judgment. I use it to stretch it. It helps me show up more prepared, ask sharper questions, and listen more intentionally. I no longer burn hours chasing baseline facts. I enter conversations already standing on second base. If you know me, you know I talk less than I listen, a rule I live by: if you’re not adding value to a conversation, don’t talk.
AI in Deal Sourcing
This is where AI has changed my workflow the most. As a self-identified introvert, outbound cold calling never came naturally, but sourcing is a numbers game. AI lets me intelligently filter that universe and focus on high-quality targets without spending every waking hour on the phone. I actually do like a portion of my week to still be spent catching up with brokers, bankers, and service providers, but I don’t have to rush through them to keep up. I can be present and enjoy the quality interactions I want to have.
Now, I can run prompts like:
· Find privately held industrial distributors in Southern California with $5–$20MM in revenue, no ownership change in 7+ years, and aging leadership teams
· Cross-reference with hiring spikes or supplier turnover
· Highlight family-run businesses in franchising or automotive services
Do I get a perfect list? No. But I get a usable roadmap, and that’s all I need to dig deeper. So far this year, I’ve screened 192 deals that loosely fit our criteria, and that’s with a lean team and a very narrow aperture. By using these tools I can quickly weed out the thousands that wouldn’t be a fit for us, and take a few minutes to take a good look at the ones that do make it to me.
AI in Diligence & Strategy
Once a target makes it past the early screen, AI helps me move fast but think deeper. With the help of custom GPTs and projects, I can:
· Map the target’s market dynamics and tailwinds
· Build competitive matrices across nearby players
· Identify potential acquirers or partners
· Flag labor risk or logistics choke points
· Surface regional tax credits or grant programs
Again, it’s not flawless, but it gets me 80% of the way there, which is more than enough to know which paths are worth pursuing, which people to talk to, and which rocks to keep turning over.
It’s like having a junior analyst, a management consultant, and a researcher in one. Nothing I’m giving it, or receiving is non public information, but trying to find it on my own or having someone else find it would take 10x longer and costs 10x more.
This Is Still a People Business
Let me be clear: we don’t invest based on GPT prompts or spreadsheets. At Alpine Ridge Partners, we back people. People who turn wrenches, solve customer problems, lead with integrity, and create lasting value. AI is reshaping how we find those people. It’s changing how we evaluate opportunities and how we scale winning businesses. It gives us more time to focus on what matters most, building authentic relationships and seeing the big picture.
Back in the day, I’d cold call off the Yellow Pages. Today, I still cold call — but I do it after talking to an AI about which questions will matter most.
The Edge: Time and Efficiency
If I have one true skill, it’s efficiency. I’ve always believed that once you eliminate wasted motion, noise, and fluff, you can zero in on what actually matters. That’s why this wave of AI resonates so deeply with me. I’m not an early adopter by nature, I prefer things with a little more humanity baked in, but this is the rare tool that multiplies my time without diluting my values.
We Invest in What AI Can’t Replace
I use AI to find companies that can’t be AI’d away. The more boring, the better. Someone still has to install HVAC systems, remanufacture transmissions, or run a specialty distribution business. Those jobs aren’t disappearing anytime soon, but the “business of doing business” around them is where AI can drive massive impact.
Most owner-operators I meet hate the admin side of their companies. They didn’t sign up to run HR, invoicing, logistics, CRM systems, or compliance reporting. They just got so good at their trade, they outgrew being a one-man shop and now have to put up with running a “business”. AI helps streamline the ops, so they can focus on what they do best. Our job is to make that frictionless.
Final Thought
AI is not the future, it’s the now. It’s not replacing people, it’s amplifying the good ones. We’re embracing this wave not because it’s trendy, but because it aligns with how we operate: cut through the noise, go deeper faster, and put people first. Let others chase hype. We’ll keep building businesses that last.